


Kiss and Tell

by goodlivin2u



Category: Supernatural
Genre: Canon Compliant, Dean Winchester is Bad at Feelings, Headcanon, Implied Sexual Content, Inspired by A Christmas Carol, M/M, Miscommunication, Trickster Gabriel (Supernatural)
Language: English
Status: In-Progress
Published: 2018-12-26
Updated: 2018-12-26
Packaged: 2019-09-27 17:56:32
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,254
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17166602
Author URL: https://archiveofourown.org/users/goodlivin2u/pseuds/goodlivin2u
Summary: Dean dresses up as Santa and kisses Cas, but Jack catches them. A family meeting causes tension to rise and the boys find that honesty is the best policy.





	Kiss and Tell

“Uncle Gabriel, angels don’t form romantic connections, do they?” Jack asked as they were seated around the table reading up on lore. The holidays had passed, and hunting was thankfully back to normal.

“Well, no. Not usually. However, if angels spend too long on Earth and grow close to their human charges, emotions may develop. It happened with Sam and I.”

“But Cas…” Jack trailed off, having a hard time deciding what to say. “Castiel is different. He has been both an angel and a human, yet he remains very logical and level-headed. I would think he’d have more humanity by now, after being with Sam and Dean for 10 years.”

Gabriel took a moment to decide what he wanted to say. With a sigh, he started: “Look, kid. Cassie’s gone through a lot to be the person he is now. You weren’t here to see his early struggles with following orders, believing in God, or the difference between right and wrong. He never fit the ‘angel’ mold, even before he became a human. However Cassie acts now is his choice and we have no business judging that.”

“I know. But maybe he should get a boyfriend. He did seem cozy with that man a couple weeks ago.”

Gabriel’s interest rose. He had been pressuring his brother to date for more than a millennium, despite it being illegal in Heaven. What were rules for, if not to be broken?

“A man, you say? Are you sure it wasn’t Dean?”

“No…” Jack replied, confused.  “It was someone else. He wore a red suit with a hat, and he had a white beard. I’ve heard stories, and I think humans call him Santa? Yes, I believe that’s his name.”

Gabe wanted to tell Jack that there was no such thing as Santa, but one look at Jack’s happy face and his resolve broke. Also, this world had far stranger things to worry about besides a weird guy asking children to sit on his lap.

“What were they doing specifically, Jack? Sitting around the fire opening presents and singing carols? It is that time of year, you know. Maybe Santa came late.”

“They were kissing, Uncle Gabriel.”

It was at this moment that Gabriel became worried. One, Cassie didn’t kiss anyone – he had learned his lesson from April. Two, kisses for the Winchester-Novak-Kline household usually involved a deal of some sort. Third and most importantly, Lucifer dressed up as Santa three years ago and they still hadn’t thrown him back in the cage. Gabe could only imagine what trouble Cas had gotten himself into…

“I’m sure it’s nothing to worry about. If Cas had wanted to tell us, he would have.”

\- - -

Later that night, Gabe talked to Sam about what Jack saw. They agreed that Gabe would take Cas on a ‘brotherly bonding’ weekend vacation and try to get to the bottom of this. Sam would stay at the bunker to maintain normalcy and check for any local demon and angel signs.

“Hey, have you noticed anything different about Cas lately?” Sam asked his brother the next morning as they drank their coffee.

“Uh…no? Not really. He seems happier, though. Good for him. Dude deserves a win.”

Dean stretched his arms above his neck, hearing some joints pop back into place. These days, hunting wasn’t kind to his aging body.

“Speaking of wins, it sounded like you’ve had several this week. I thought we decided not to bring home one-night stands anymore, Dean. Bad for the kid,” Sam gestured with his head to the next room where Jack was taking down Christmas decorations.

“Oh, right. Sorry…I guess I forgot. Oops?” There wasn’t a trace of regret in his voice, though.

“It’s okay, just don’t do it again. We have to be better, _do_ better now. Isn’t it time that we grow up? We’re not hormone-driven teens anymore.”

“Fine. Yeah, got it: be quieter when Jack’s in the house.”

“Dean!”

“Sammy, I’m pretty sure Jack knows that sex happens, and it’s not always between two people madly in love such as you and Gabe. It’s just a fact of life. Maybe _you_ should be the one to grow out of your idealism,” he grumbled as he grabbed his _and_ Sam’s coffee cup (because he’s a jerk), slamming his bedroom door down the hall.

“Well, that went well,” Sam mumbled to himself.

\- - -

Gabe had spent the better half of the weekend trying to see if Cas had been possessed. None of the usual tests worked, but then again, this was Lucifer they were talking about.

“So, Cassie… what’s new with you? We haven’t properly caught up in ages! Anything interesting you want to tell me?”

Cas leveled his brother with a glare. “No, Gabriel. I’ve been quite busy lately, if you haven’t noticed.”

“Busy doing what, baby bro? Look around: the world isn’t burning at the moment. No one needs saving.”

“I’m trying to repopulate Heaven, since you’re not interested in helping these days.” Cas shot Gabe a patented Winchester bitchface #56, one of his personal favorites.

Gabe wiggled his eyebrows. “Ooh, _repopulating_! Making babies over there? Having hot, steamy sex?”

“I think you’ve been reading too much of Becky’s fanfiction.”

“Hey! That stuff’s based in reality. I should send that girl a fruit basket, come to think of it!”

“ _Anyway_ … it has proven to be a difficult task, thanks to the fact that both you and Lucifer have refused.”

“What about Jack? As a nephilim, he has enough power.”

“I couldn’t ask that of him. Not right now, at least. I have to act fast, before Heaven disappears. I haven’t found a sustainable, long-term solution, though.”

“You’re not doing something dangerous, though…are you?”

“No, Gabriel. If I do anything stupid, I’ll let you know.”

\- - -

A couple weeks later:

“Hey Samsquatch! Have you seen the apple pie leftovers from last night?” Gabe called out into the bunker, not knowing exactly where his human was. There was no response, so Gabe used his heightened sense of smell to find the answer.

His search led him to Dean’s room. Without so much of a knock, he barged in.

“Dean, did you take – OH MY DAD!”

Dean looked up from where he was situated between Cas’ legs on the bed. Traces of pie could be seen on both of their chests, and Dean had the remains of a whip-cream beard.

“Well,” Gabriel huffed. “I guess Santa did come after all!”

\- - -

As soon as Dean and Cas cleaned up and got dressed, they had a family meeting. Thank goodness Jack was away on a hunt with Mary, because this was definitely a conversation for grown-ups.

“We didn’t want you guys to find out about this like you did,” Cas started.

“And what exactly is ‘ _this_?’”

Dean grumbled “Not what it looks like,” under his breath. His arms were crossed defensively against his chest, his expression equally angry and mortified.

“How about you tell us, Cas?” Sam suggested with a smile. He had always secretly been a fan of Destiel, and hoped his brother had finally manned up and told Cas his feelings.

“Well... I have been looking for ideas on how to repopulate Heaven, as you know.” The group nodded along. “One of the ways is to create more nephilims, via angel copulation with a human. That option became harder once I couldn’t find a suitable partner to carry the infant to term – namely, a woman.”

“Cassie, I’m sure there are more than enough women on any street corner in this town.”

“Gabe – “ Dean warned. Just because some women were sex workers, didn’t mean that consent wasn’t important.

Cas continued: “Because of this, I talked to Naomi about my predicament and sexual attractions.”

Clapping his hands together, Gabriel exclaimed: “Oh, how I wished I could have been a fly on that wall. To see her face… it would have been priceless! I could die a happy man.”

“GABE!” Both of the Winchester brothers yelled.

Cas waited. “To say she wasn’t thrilled would be an understatement, but we discussed other remedies. She told me that I could have sex with a man instead, and a nephilim would still be produced. My grace and my partners’ semen, added with fragments of their soul, could create a ball of energy inside of me. Afterwards, I would visit Heaven and they would extract the combination, housing it in one of the laboratories there until it matured into a full-fledged offspring. I hear that the process is similar to when human eggs and sperm are in a petri dish, or when a premature baby is born and placed in an incubator. From then on, Heaven – namely, Naomi – will take care of the new nephilim for the rest of its existence.”

“Okay, so how did you get from re-populating Heaven to having Dean suck you off with MY apple pie?” Gabe asked.

Dean tried to telepathically tell his brother ‘ _control your boyfriend_ ,’ but all Sam did was shoot him an apologetic look and a mere shrug. Finally, the younger Winchester spoke up: “Gabe, how about we keep the graphic descriptions to a minimum? They’ve been through enough today,” he said, trying to hold back a laugh. His eyes betrayed him, though.

Throwing his hand over his heart in mock hurt, Gabe gasped. “But Samsquatch, I thought my diverse vocabulary was one of your favorite things about me!”

“It is,” Sam hissed from the corner of his mouth. “But keep it in the bedroom.” He cleared his throat. “Sorry, Cas. You were saying?”

“Yes. Well, I was explaining my predicament to Dean one day, and he offered to help.”

“ _’Offered?_ ’ More like I told him “ _Buddy, you know I would help if I could, but…_ ’” Dean said.

Cas turned toward Sam. “I told him that there was a way he could contribute – “

“Gee, Cas. You don’t have to make it sound so clinical! We did have sex after all.”

“- and he was amenable to trying. We went through the necessary steps, created a decent amount of offspring, and then we realized we didn’t want to stop.”

“Wait, Dean…I thought you told me you didn’t want any more kids after what happened to Ben and Emma?”

“Funny you should mention Emma, Sam. You know, I would still have her IF YOU DIDN’T SHOOT MY ONLY DAUGHTER. I mean, really, Sam! A teenage girl is harmless.”

Gabriel piped up: “Have you met Claire? She’s a teenager and even scares poor little me.”

“Not helping, Gabe!” they all shouted in unison.

Sighing, Sam said: “Dean, she was a monster. She came to your hotel room to kill you. It was only a matter of time.”

“MY ONLY DAUGHTER, SAM!!” Dean was getting out of his chair now, vein in his forehead threatening to burst. Cas struggled to pull him back.

“Anyway,” Cas began again, “Dean is a wonderful parental figure to both Claire and Jack. I would hopefully be correct in my assumption that he would continue to be a good role-model for these nephilims, should the need arise.”

“But it won’t, right?” Sam asked. “These nephilims will, in a way, truly be children of God. Or Heaven, more accurately. But Dean won’t have any parental responsibilities to them.”

After a moment of consideration, he said. “Huh. Yeah, I can see the appeal. It makes sense that Dean agreed to that. So are you two like, together-together now?”

Dean and Cas looked at each other, one replying “Yes,” while the other answered “No.”

“Obviously you two lovebirds have things to discuss. I think this would be a good time for me to leave.”

“Sit your ass down, Gabriel,” Dean ground out. “We wouldn’t be in this mess if it weren’t for you.”

“What did I do?” Gabe asked innocently.

“You wouldn’t help power Heaven when the angels needed you – when your own _brother_ needed you – so he had to find another solution. Does family mean nothing to you, Gabe?”

“Dean,” Sam said quietly.

“Really, though. I know angels call each other brothers and sisters, and we joke about Chuck being Dad, and you guys say how you would die for each other, but there’s actually more angel-on-angel deaths than any caused by humans or other monsters. Your words mean nothing without action, Gabriel. I hate to say it, but humans are better than angels in one respect: we care about each other, even if we’re not blood-related. In this profession, we don’t get much of a happy ending, so we take what we can get. My family may be small, and most definitely broken, but there’s a whole lot of love here.”

“Yes,” Cas speaks up, proud of the human he secretly refers to as his. “Knowing I had Sam and Dean as a support system definitely made my fall from Heaven and transformation into a human more bearable. I’ve learned so much from them, and I think you have too, Gabe. Being strong doesn’t mean being selfish or being alone. Our strength comes from relying on others and sharing the common struggle.”

“I guess I could see what I can do to help,” Gabe says.

“It’s all we ask of you.”

Dean perked up: “Oh and Gabe? Remember this: ‘ _do or do not, there is no try_.’”

Sam smacked his brother on the backside of his head, saying “Ignore him” before going to his room. Just as his door shut, the front one to the bunker opened.

Mary yelled “We’re home!” and Dean thought, _yes_. Yes, they were.

**Author's Note:**

> I know I didn't really tie in the whole "Daddy kissing Santa Claus" bit that was the original inspiration for this, and I know I need to talk more about Lucifer, and I definitely need to answer the huge question "What happens to Dean's soul?" in this headcanon. So I have decided to write another chapter! But I wanted to post this one before the holidays were over. I hope you enjoyed it!


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